Organizations today live in a complex business landscape that requires them to be increasingly resilient, resourceful, intuitive, and flexible. Organizations must confront increasing complexity, turbulence, unpredictability, and the speed of change in the competitive environment. Many different forces and trends are shaping the new business landscape, and rapidly evolving digital technologies are forcing breakthrough and disruptive innovations. For companies to survive and thrive, they must transform their business and behaviours to respond to the evolving business landscape and turn challenges into opportunities for development and growth. Unlike change management, transformation aims to reinvent the organization and encourage the adoption of new approaches and discover new or revised business models that shape the perceived vision of the future. In particular, it is a digital transformation: the current business landscape is characterized by a continuous and inevitable digital evolution, so any type of organization should adopt the transformation considering digital factors. In this perspective, companies need to generate, manage and leverage tacit, explicit and practical knowledge to drive transformation and remain competitive. Creating a transformation culture is not easy and many factors contribute to this outcome. Leadership represents one of the critical catalysts of a transformation-focused organizational culture. Transformative leaders today are responsible for fostering an organizational cultural mindset that aims to support and encourage transformation. For this reason, it is important to attempt to identify and measure the critical competences that drive and facilitate the generation, management, and use of knowledge for continuous innovation. The study is at a preliminary stage and focuses on the following imperative research question, “How are the competences assessed that lead a Transformative Leader managing an organization to continuously innovate and drive transformation considering the digital age?”. Proposed is the Transformative Leadership Assessment Framework, a first draft of a competency model to assess the characteristics of leaders who drive organizational transformation in today’s complex business landscape. It lays the foundation for defining the specific skills, knowledge, and behavioural requirements that enable a leader to be transformative and lead an organization toward continuous innovation. Competences provide individuals with exemplary performance that has an appropriate impact on business outcomes. This analysis helps specify a set of useful behaviours of transformative leaders, provides a tool that individuals can use for self-development, and outlines a leadership framework that can be used by to select, develop, and understand the effectiveness of transformative leaders in transformative organizations. To develop the Transformative Leadership Assessment Framework, the principles of grounded theory were adopted and, using secondary data such as recorded interviews, the authors examined the profiles of some of the most influential and inspirational modern tech leaders.